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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 40, 2010 - Issue 22
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Original Articles

Divergent Products Obtained from the Reactions of Salicylaldehyde and 4-Hydroxycoumarin in TEBAC-H2O, KF-Al2O3-EtOH, and Ionic Liquid

, , &
Pages 3332-3345 | Received 15 Apr 2009, Published online: 15 Oct 2010
 

Abstract

Controlling selectivity of the reactions of salicylaldehydes and 4-hydroxycoumarin in triethylbenzylammonium chloride–H2O, ionic liquid, or KF-Al2O3-EtOH systems, respectively, resulted in the syntheses of three series of different coumarin derivatives.

ACKNOWLEDGMENTS

We are grateful to the National Natural Science Foundation of China (20802061), the Natural Science Foundation (08KJD150019), and the Qing Lan Project (08QLT001) of the Jiangsu Education Committee for financial support.

Notes

a Reagents and conditions: salicylaldehyde 1 (0.122 g, 1 mmol), 4-hydroxycoumarin 2 (0.324 g, 2 mmol), solvent (10 mL).

b Isolated yields.

a Reagents and conditions: 1 (1 mmol), 2 (0.324 g, 2 mmol), KF-Al2O3 (0.102 g, 1 mmol), and EtOH (10 mL).

b Isolated yields.

a Reagents and conditions: 1 (1 mmol), 2 (0.162 g, 1 mmol), TEBAC (0.023 g, 0.1 mmol), water (10 mL).

b Isolated yields.

a Reagents and conditions: salicylaldehyde 1 (1 mmol), 2 (0.324 g, 2 mmol), and [BMIM]Br (2 mL).

b Isolated yields.

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